


The Masks We Wear

by chibi_nightowl



Series: Adventures in Crossdressing [2]
Category: Batman (Comics), Red Robin (Comics)
Genre: Character Study, Costumes, Crossdressing, Gen, Tim is a pool shark
Language: English
Status: Completed
Published: 2017-07-20
Updated: 2017-07-20
Packaged: 2018-12-04 12:01:24
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,808
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11554791
Author URL: https://archiveofourown.org/users/chibi_nightowl/pseuds/chibi_nightowl
Summary: Tim plants the butt of the pool cue on the ground and places a hand on his hip, jutting it out ever so slightly in a challenging pose as he looks around the small group of people around the table. “Anyone else want to give me a run for my money?”“I will,” a familiar voice drawls lazily from the other side of the pool table. Jason leans against one of the high top tables, a bottle of beer in one hand and a half finished cigarette in the other. He blows smoke in Tim’s direction, leering slightly. “Lookin’ good there, pretty bird.”





	The Masks We Wear

**Author's Note:**

  * For [Firestar385](https://archiveofourown.org/users/Firestar385/gifts).



> For Firestar385...I have a feeling this may not be exactly what you had in mind, but this is how I perceive Tim and his views on crossdressing. I hope you enjoy it!

Tim peeks around the corner of the alley, watching the man he’s been tailing for the better part of the night enter the rough looking bar on the edge of Crime Alley were it borders with New Town. Motorcycles are parked out front, and there’s a steady enough stream of people going in and out that sneaking in and hiding in the shadows won’t work. Normally, he’d have taken the man, Ronnie Sims, down already for his crimes, but he’s hopeful that Sims will lead him to the next player further up the food chain. There’s a new drug on the street and Tim wants to cut it off at the source rather than deal with the bit players.

Glancing down, Tim grimaces, knowing he’s not anywhere close to being appropriately dressed to just waltz into Scratchers. Costumed vigilantes aren’t exactly welcome here.

He glares at the door of the bar, not happy with the decision he’s just had to make. Still, Sims has come here twice out of the last three nights. It’s the only logical place for the swaps to occur.

Tim sighs in frustration and steps back into the concealing shadows of the alley. He’s got work to do so that he’s ready for tomorrow night.

*****

The next afternoon, Tim showers carefully, trying to get into the right mindset for the performance he’s about to get ready for. Unlike Bruce who’s just flat out awkward when it comes to cross-dressing, Tim looks at it as an art form. There’s something to be said for the skill it takes to convince the world that, at least for the moment, he’s a woman.

Alfred had taught him the use of makeup and padding, as well as what kind of clothing would work with his slim, but still masculine form. He would never be as tall as his brothers, Jason, or Bruce, nor would he ever be as broad across the shoulders. His muscles are compact, lean strength that, coupled with his speed, make him a formidable opponent. Always thinking. Always analyzing.

And what his analysis of the situation told him is that dressed as a man, Tim would get eaten alive in that bar, no matter what disguise he put on. But if he were to completely _change_ , well, there’s certainly something to be said that he could pull the wool over everyone’s eyes.

When he’s done in the shower, his first task is shaving. Legs, underarms, his chest, even the fine trail of hair that normally disappears into his briefs. He briefly considers shaving even lower, but decides against it. If anyone gets _that_ close, then he’s screwed already.

The hair on his forearms he bleaches, then trims down.

By the time Tim is done with everything, he’s gone through two razors he’d bought specifically for this purpose.

He turns his attention to his reflection in the mirror over his bathroom sink. He makes a face and grabs his tweezers to start shaping his eyebrows into something more feminine looking. Tim isn’t going for fashion or style, but he is glad that pencil thin eyebrows are no longer quite as common as they used to be.

All the while, he thinks about the mask he’ll be putting on soon.

For all that his family jokes that Tim’s always the one who has to put on a dress when the situation calls for it (and Steph isn’t available to help out), he doesn’t really mind. It’s a mask, a costume, a part to play for the mission. If he plays it right, he wins the prize and the bad guy goes to jail. The mask comes off when he gets home and then he’s Tim Drake once again.

Still, as Alfred is always wont to say, even a costume is only as good as the character behind it. Jason certainly proved that when he created his drag queen persona.

So Tim thinks about the character he’ll need to play tonight. She needs to be tough to walk into a bar like Scratchers on her own. Confident, but not too much as she has to ingratiate herself with his target and let him lead her to the next one. She also has to be attractive and sexy, especially with the limitations his body will afford him with his wardrobe choices. No plunging necklines here, no cleavage to flaunt.

He’s got a really good bodysuit that he’s worn before under dresses that give him the illusion of having curves instead of the flat planes of his highly trained body. Depending on what shirt he decides to wear later will determine which bra and falsies he’ll add into the mix.

Finally pleased with his eyebrows, Tim shaves the rest of his face with his regular razor. Unlike Bruce and Dick who both sport rather obvious shadows on their faces by the time patrol rolls around, he can still get away with shaving every other day.

Tim exits the bathroom and heads into his bedroom. Opening his closet door, he stands in front of the full length mirror and drops the towel from around his waist, inspecting every inch of his body to make sure he’s shaved and tweezed all the right places. Satisfied with what he sees, he pulls a trunk out of the closet. In it is his body suit, which he puts on, as well as his gaff, carefully tucking himself away as he slips it on. There’s a trick to it, which took more time to study through the help of YouTube than Tim would care to admit.

When Jason had learned the extent Tim would go for his adventures in cross dressing, his eyes almost bugged out of his skull. “You’re not as boring as you seem, Drake,” he’d said without the usual sarcastic sneer he almost always has around him.

High praise coming from the former Robin.

Once everything is in place (and some carefully added padding at his hips and over his rear giving him the illusion of curves Tim most certainly doesn’t have), it’s time for wardrobe.

Fishnets are rolled up his smooth legs and clipped to his garter belt. He’ll purposefully rip them in a few places before he leaves.

Laid out on his bed is his outfit for the night. He’d found a high-waisted red and black plaid mini skirt at the thrift store he went shopping at earlier in the day that was perfect. Slutty, but not overly much, the tops of his fishnets just peeking out from under the hem. Tim stares at the three tops he purchased, still unable to decide exactly which one would work best. They would all work with the military style black bolero jacket he already owns.

Sighing, he looks over at the clock. It’s almost seven. Sims usually makes his appearance at Scratchers after ten, but no later than eleven.

Tim takes the different sets of falsies and bras out of the truck and starts playing dress up to decide which combination works best.

Go figure it’s the white scoop neck tank top with the red bra. A C-cup is the largest he’ll go; anything else just makes him look top heavy and off balance. Tim rolls his eyes as he returns to the bathroom to do his hair and makeup. For once, his overly long hair comes in handy as he wets it down, then runs his fingers through it with some styling mousse to create a wave-effect. A couple of small hairclips later and he’s done.

His makeup is trickier, but he’s done this so many times now that he doesn’t hesitate. Stephanie loves it when they have to dress up together as she swears up and down that he’s a better hand with eyeliner than she is.

“Nerves of steel,” he always jokes.

“Too bad Dick has the buns of steel, nerd wonder,” she would tease back.

It takes a deft hand to soften his jawline without the use of prosthetics, but he makes sure his lips are full and _red_ so as to draw attention away. The dim lighting in the bar will help, but always best to be prepared.

There’s nothing he can really do for the bump that is his Adam’s apple other than to hide it behind a choker. It’s not overly prominent like some men’s are, but it is noticeable.

Tim then turns his attention to his hands. Long fingers, short nails, scarred knuckles. Not exactly the most attractive hands, at least in his opinion.

False nails are added to the costume and painted black. When they’re dry, he chips them in a few places to give them a more worn look, like he hadn’t just done them. His knuckles are hidden under a pair of fingerless leather gloves that work well with the outfit.

Calf high black leather boots are added to the ensemble. He puts on his jacket and stands once again in front of the mirror.

Tim grins, pleased with how everything turned out. “Now I just need a name…” he mutters, turning around and looking over his shoulder at his backside. The skirt flares out slightly just under the curve of his padded bottom.

Red lips twist into a smirk. “Rachel will do.”

It’s time to get to work.

*****

Tim sits at the bar, nursing a bottle of cheap beer that tastes like piss. He’d rather drink from the bottle than the glasses he’s positive any health inspector would take one look at and freak out over. Not that there’s much of anything in here that would pass a county health inspection, he muses.

He’s early, but considers it for the best. Plenty of time to scope of the interior of the bar and work out any escape plans in case he needs to make a speedy exit. There’s a door on the far end of the bar that Tim suspects leads to some kind of backroom where there’s more action to be found. There’s also a very obvious meathead standing by said door, so he’s not going to be able to just wander in either.

It’s time to garner some attention. Time to put his acting chops to the test.

Tim catches the eye of one of the younger bikers who’d just wandered in and gives him a small smile, a slight twist of the lips that promises so much of something he has no intention of delivering on.

Hooked. The young man wanders over, a cocky grin on his face as he leans against the bar next to Tim. “Hey there, good lookin’. Haven’t seen you in here before.”

He’s not bad looking, Tim decides as he starts a stream of flirty small talk. A shower and shave would do him good, not to mention a haircut. His arms are covered in tattoos, almost full to the point where he could be said to have sleeves.

A few minutes later finds them at the pool table racking up for a game. It’s just opposite of the door that has captured Tim’s attention, which had been his intention when he asked if the guy played.

It’s all too easy to beat him. A single game turns into best two out of three, which Tim handily wins. They’ve attracted a bit of a crowd, with money changing hands with loud raucous laughter at the biker’s expense each time he wins.

“Sorry, honey,” Tim purrs as he gives the man a wide-eyed and innocent look. “My Daddy taught me to play.”

“He taught you good,” the guy replies with a grin.

Tim plants the butt of the pool cue on the ground and places a hand on his hip, jutting it out ever so slightly in a challenging pose as he looks around the small group of people around the table. He’s pleased to see he has the attention of the lug-head bouncer and winks at him. “Anyone else want to give me a run for my money?”

“I will,” a familiar voice drawls lazily from the other side of the pool table.

Looking over his shoulder, Tim clamps his jaw shut as he spots Jason leaning against one of the high top tables, a bottle of beer in one hand and a half finished cigarette in the other.

He blows smoke in Tim’s direction, leering slightly. “Lookin’ good there, pretty bird.”

There is no doubt in his mind that Jason knows who he is, not with what he just called him. It’s a damn sight better than baby bird at least.

“Sure you can keep up with me?” Tim replies archly.

“Give it my best shot.” Jason takes another drag on his cigarette and stubs it out in the ashtray behind him.

The biker gloomily hands over the pool cue he’d been using and steps to the side.

Tim racks the balls, making sure he puts on a show. He had told Jason how he’d gotten to be so good with makeup when they were putting together his drag queen outfit. Hell, Tim had done his makeup every night until they finally caught the man behind the assaults. It was a way to fill up the time, or so he tried to tell himself afterwards, but he knew he was lying to himself.

He and Jason had found something to _bond_ over. It was a first for them.

Jason’s interest in crossdressing was more along blurring societal gender norms, but he’d been fascinated by Tim’s stories of just how he’d gotten to be so good at this. Learning from Alfred had been just the tip of the iceberg.

It gives Tim a small thrill to have Jason see him here, dressed like this. To appreciate the time and effort it took to make all this happen and not tease him about it.

More importantly though, Tim wonders why the hell Jason’s here at all. He has a sneaking suspicion his case is overlapping with something the other man’s working on.

But with the crowd around them now, it’s impossible to find out. Tim does his best to keep an eye on the front door for Sims and beat Jason at the same time. It’s obvious that the former Robin is not holding back, power-housing through the break.

“Stripes,” he calls out.

“Fine by me,” Tim grins as he walks around the table to walk his fingers up the brown leather sleeve of Jason’s jacket. “I like solids,” he says and leans in, looking for all the world like he’s trying to distract Jason from his shot. “I’m here for Ronnie Sims,” he breathes into the man’s ear.

Jason easily sinks his shot. “Nice try, babe,” he says as he steps out of Tim’s space and around the table for his next shot. “Corner pocket.” He uses the tip of the cue to indicate the striped blue number ten ball and the intended shot.

He makes it, but misses the next one, turning the game over to Tim. This time, Jason walks around the table, crowding into his space. “Turnabout is fair play,” he says as he runs a hand down the length of Tim’s back.

“Side pocket,” Tim replies and sinks the solid blue number two ball. “Looks like no more blue balls on the table.” He stands up straight, right in the curve of Jason’s arm.

Jason takes the opportunity to lean in, the cocky grin on his face making it look like he’s saying something dirty in reply. “Mikey Harris,” he whispers. “I need to get in the backroom.”

Different people, same goal.

Tim smiles slyly as he steps out from Jason’s half embrace. They’re playing this flirting game for all it’s worth and the people around them are eating it up. “You just might if you play your cards right. Let’s see how things work out.”

*****

Things actually work out rather well for the two of them. Sims is a no show, but Jason’s guy makes an appearance, grabbing a beer from the bar, then heading straight to the back. It’s where Tim wants to be anyway, so he takes it as a win.

Tim manages to attract the attention of the lug-head bouncer who appreciates a fine looking ass bending over a pool table. With some careful flirting and another promise he has no intention of keeping, he gains him and Jason entry into the back.

It’s definitely a drug den. What concerns Tim the most is that they’re dealing in the new designer drug he’s been trying to trace back to the supplier. The drug heightens euphoria and lowers inhibitions, but a dangerous side effect is that it causes cardiac arrest. He’s aware of at least five people who’ve died because if it.

From the looks of it, Jason’s on the same page he is as Mikey Harris appears to be another dealer. Tim manages to get a good picture of the man he gets his package from and plans to spend some quality time with his facial recognition program when he gets home to get a name. Jason scores them a sample of the drug, which Tim’s been itching to get his fingers on.

All in all, it’s a good night. He’d managed to win about a hundred bucks sharking people at the pool table too.

They’ve been flirting with each other all night, so it raises no suspicions when they leave together. Jason had ridden one of his (mostly) street legal motorcycles here, so Tim hops on the back and they drive away.

Before long, Jason’s pulling up in front of Tim’s apartment in the heart of Crime Alley. There’s a small garage off to the side, which Tim directs him to park in rather than on the street.

“Well, that was quite the adventure,” Jason comments as he follows Tim inside. “I didn’t recognize you at all until you started wiping the floor with that first guy.”

“So you were already there when I arrived?” Tim asks as he sits down on the sofa to take off his boots. His feet hurt.

“Yeah. Gotta admit, this all turned out better than I’d hoped for tonight.”

Tim starts rubbing his feet. “Agreed. I’m trying to trace that drug back to a supplier and cut off the flow at the source. You?”

“Same,” Jason replies. He’s staring curiously at Tim.

“What?”

Jason shrugs. “It’s just…” he starts laughing. “You make a really hot chick, Drake.”

“Thanks.” Tim rolls his eyes. “I’m about to overheat with all this padding and latex though, so if you don’t mind, this get up is coming off.”

“Go right ahead. Don’t take this the wrong way, but can I watch? I’ve never seen that good of a body suit before.” He sounds hesitant, like he’s asking something _too_ personal.

Tim doesn’t mind at all. “It doesn’t bother me. It’s just a costume.”

Jason follows Tim upstairs and into his bedroom. He keeps his distance, leaning against the doorframe as Tim removes his clothes and starts peeling off pieces of his padded suit. He makes a point to throw the bra and falsies at him though, just to see his reaction.

“What the hell?” Jason fumbles as he catches them. “Whoa, these are really good.” His eyes widen in surprise as he pokes at the fake boobs.

“It’s all part of the act. The way I look at it, if I’m going to dress as a woman, I may as well go all out.”

“But it’s not something you like doing, right?” Jason tosses the bra onto the bed.

“No,” Tim replies as he sits down to remove his stockings. “I’m a guy. I most definitely identify as a guy and have no desire to wander around in women’s clothing. This is a costume. An act. If I do it right, I get what I want in the end and that’s that.”

“So you’re not embarrassed at all by all this?” Jason gestures to the now obvious padded suit Tim’s starting to remove.

“Why should I be?”

Jason shrugs. “Most guys are. Look at Bruce.”

“Bruce did what he had to, which worked out well for him last time because he needed to play the uncomfortable card. It just worked out better for us that our guy was more into you.”

“That was a ton of fun,” Jason agrees. “Probably the highlight of my year was seeing Bruce’s face when we walked into the Cave that first night.”

Tim laughs. “Mine too.”

He’s down to just the gaff now, which he will _not_ remove in front of Jason. He lays the body suit out on the bed. “I’m going to grab a quick shower to clean this crap off. Feel free to poke at the suit.” Tim grabs a clean pair of boxers and a t-shirt and disappears into the bathroom.

Jason is still exploring his body suit when he comes back. “This is custom made, right?” he asks. “But you can also add and remove padding if needed.”

“Right. Alfred helped me make it. I’m the only one of us who can pull this kind of thing off.”

“No shit. I’ll stick with being a drag queen.” Jason turns his attention back to the freshly showered Tim. “Looks like Rachel’s disappeared down the drain.” He grins.

“Yeah, but I can put her back on if needed. I like to create a character for each costume,” Tim explains as he picks up the suit and lays it out over his trunk. It needs to air out before he puts it away. “Rachel’s fun though. I think I’ll keep her.”

“I liked her, too bad she’s not real.” Jason winks at him. “A pool shark like her is a keeper.”

“Anytime, any place,” Tim replies, not even missing a beat. “Want to come downstairs with me? We can start an analysis on that drug and run the picture I got through facial recognition.”

“You sure know how to sweet talk me, Replacement. I take it we’re working this case together now?” Jason follows Tim out of the room.

“Why not? We’re both after the same thing,” he replies as they head downstairs.

“Fair enough,” Jason agrees. “Question for you.”

“What?” Tim punches in the code for the secret entrance leading down into his workroom.

“Halloween’s coming up here soon…wanna freak out Bruce by showing up somewhere he is dressed in drag?” There’s a hopeful note in Jason’s voice that Tim can’t help but pick up on.

Tim grins over his shoulder at Jason as they descend into his workroom. “I don’t dress in drag,” he replies archly. “But with enough time, we can put together an even better outfit for you.”

“As long as I get to wear those boots again, you can do whatever you want to me. After what I saw tonight, I’m a believer.”

“I want pictures.”

“Deal.”

 

**Author's Note:**

> To be perfectly honest, I'm not a huge fan of how feminized Tim is often portrayed in fanfiction. I get it, I really do, but I have a hard time wrapping my mind around the fact that a young man as highly trained as him doesn't have some muscle to show for it. No, he's not anything like his brothers, not at all, but he's still a guy.
> 
> I also spent way too much time researching the actual transformation process using the type of costume Tim has. Educational to say the least.


End file.
